General Organic Chemistry - careerendeavour.in · General Organic Chemistry 5 Problem : The correct order for the stability among following compound is CH 3 CH 2 H 2 (II) (III) CH

1General Organic Chemistry

1.1 Introduction:Organic reaction involve the breaking and making of covalent bonds. The breaking and making of covalentbonds usually occurs in several descrete steps before transformation into product. The detailed sequentialdescription of all steps of the transformation into products is called the mechanism of a reaction.

Complete information regarding all the steps is seldom obtained. However, a good deal of data can begathered from the following(a) study of kinetics of the reactions(b) isolation of intermediate, if isolable.(c) study of reactions in the presence of other similar substrate.(d) study of the isotopically labelled atom in the reactants.(e) trapping of free radicals(f) crossover experiments(g) stereochemical aspects etc.

Reaction mechanism containing following tools

solventtemperature/light

pressureReactant

#

Intermediate

Transition stateOR

Product

(i) Reactant :Reactant are classified into substrate and reagent(A) substrate species at which reagent attack.(B) Reagent attacking species (more reactive species)

Case-I: If reaction occurs between organic and inorganic species, organic species act as substrate and inor-ganic species act as reagent.

substrate reagentOrganic species Inorganic species Product

Case-II: If reaction takes place between organic species then higher charge species act as reagent, otherspecies act as substrate.

less charge excess chargesubstrate reagent

Organic species Organic species Product

General Organic Chemistry

1CHAPTER

2 General Organic Chemistry

Example:H3C CH2 CH2 Br + KOH H3C CH2 CH2 OH + KBr

substrate reagent(organic) (inorganic)

product

H3C CH2

CH

O

(substrate)

+ H2CC

CH2

O

CH3

H3O+

(reagent)H2C

CHH3C

OH

CH2

C

O

CH2

CH3

1.2. Electrophiles :(Electron loving species) electrophiles are electrons-deficient species and tend to attack the substrate at a siteof high electron density. They may be neutral species as examplified by Lewis acid (such as BF3, AlCl3, ZnCl2),carbene and carbocations.

HProton as electrophiles

+ OHhydroxide ionas nucleophile

HO

Hwater

Classification of electrophiles:(a) Species having positive chargeExample : 2 6 5 2 3H , R , Cl , NO , NO , C H N , CH C O etc.(b) Neutral species having vacant p-orbitalsExample : BF3, BCl3, BBr3, carbene, etc.(c) Species having vacant d-orbitalExample : FeCl3, ZnCl2, FeCl2 etc.(d) Species having low lying -antibonding molecular orbital.Example : Br2, Cl2, I2 etc.(e) -bonding molecule:

Example : SO3, CO2,O

R C N, , ,

O

etc.

(f) Element in their atomic state :Example : O, S etc.

1.3. Nucleophiles:(Nucleus-loving species) Nucleophiles are electron donar species. Nucleophilic reagents tend to attack theelectron deficient species (electrophiles).

Classification of Nucleophiles:(a) Negative charge species:

OH ,OR ,SH ,SR , R ,Cl , Br , I etc

(b) Organometallic reagent:

2 2 2R MgX, R Li, R CuLi, R Cd, R Zn etc

(c) Lone pair containing species:

H2O , R O H , NH3 , H2S ,

N

etc


(d) -bonded molecules:

Alkene, Alkyne, Benzene, OR

,OH

,

N

etc

Note: Some species behave as the electrophiles as well as nucleophilesExample : Br2, Cl2, I2, etc.

Ambidentated nucleophile : Those nucleophile which posses more than one site for E+ attack but at thesame time only one side is used to form bond with electrophile. It is called ambidented nucleophile, such typeof ambidentated nucleophile are regioselective.

Example : H2CC

O

HH2C C

O

H

O

+ R X

O R

+ X

O

+ R X

O

+ X

R

Note: Decreasing order of nucleophilicity

[Electronegativity % of S-character]

Note : Electron Displacement Effects:Effect occuring due to displacement of electron in organic compound is called Electron DisplacementEffect or electron delocalisation effect.Electron displacement effect is of mainly two types.

Electron Displacement Effect

Permanent effect(Polarization effect)

Temporary effect(Polarizability effect)

Inductiveeffect

Hyperconjugation

Resonance Mesomericeffect

Inductomericeffect

Electromericeffect


Other Effect:(a) Steric inhibition of resonance (b) Ortho effect.

1.4. Inductive effects:In a covalent bond between two different atoms, the electrons in the bond are not shared equally. Theelectrons are attracted towards the most electronegative atom. An arrow drawn above the line representing thecovalently bonded electrons shifts towards higher electronegative atom can show this. Electrons are pulled inthe direction of the arrow.

When the atom (X) is more electronegative than carbon

electrons attracted to X

C X

negative inductiveeffect (–I effect)

When the atom (Z) is less electronegative than carbon

electrons attracted to carbon

C Z

positive inductiveeffect (+I effect)

–I groups +I groupsX=Br, Cl, NO2, OH, OR, SH,

SR, NH2, NHR, NR2, CN, CO2H,CHO, COR

Z=R(alkyl or aryl),metals (e.g. Li or Mg)

The more electronegative the atom(X),the stronger the –I effect

The more electropositive the atom (Z),the stronger the +I effect.

Pauling electronegativity scale

K = 0.8C = 2.5N = 3.0O = 3.5

I = 2.5Br = 2.8Cl = 3.0F = 4.0

Higher the value, more electronegative will be atom

The inductive effect of the atom rapidlydiminishes as the chain length increases

H3C CH2 CH2 CH2 Cl

experiences a negligible –I effect

experiences a strong –I effect

The overall polarity of a molecule is determined by the individual bond polarities, formal charges and lone paircontributions, and this can be measured by the dipole moment (µ). Higher the dipole moment (measured indebyes (D)), more polar will be compound.

1.5. Hyperconjugation:A bond can stabilise a neighbouring carbocation (or positively charged carbon) by donating electrons tothe vacant p-orbital. The positive charge is delocalised or ‘spread out’, and this stabilising effect is known as“no-bond resonance”.

C–H-bond

vacant p-orbital

HThe electrons in the -bondspend time in the vacant p-orbital

Points to Remember :Number of hydrogen number of hyperconjugating structure stability

1 1Polarity dipole moment Heat of hydrogenation bond length


Problem : The correct order for the stability among following compound is

CH3CH2 CH3CH2CH2

(III)(II)

CH CH2

H3C

H3C(II) (IV)

C CH2

H3C

H3C

H3C

(a) I > II > III > IV (b) I > III > IV > II (c) IV > III > II > I (d) IV > III > I > II

Soln. Number of hydrogen stability..

Thus,

CH3CH2 CH3CH2CH2

(III)(II)

CH CH2

H3C

H3C

(I) (IV)

C CH2

H3C

H3C

H3C3 2 1 0Number of hydrogen

Stability, I > II > III > IV

Hence, option (a) is correct.

Problem : Which is more stable methyl -D glucopyranoside or methyl -D glucopyranoside.

O

OCH3

HO

H

OCH3

Methyl -D glucopyranoside Methyl -D glucopyranoside

orbital

axial lone pair

(axial-axial interaction is more feasible)

There is stabilising interaction i.e. hyperconjugation between the unshared pair on the hetero atom and *orbital for the axial C–X bond in the case of anomer. thus it is more stable as compared to its analoguein which there is no such interaction.

Note : If oxygen is replaced by carbon, there is no such stability interaction as like as above. Thus, stability canonly be decided on steric ground. Thus stability order for such species will be

OMe >>

OMe(Stability)

1.6. Mesomeric effects:Whilst inductive effects pull electrons through the bond framework, electrons can also move through the

bond network. A bond can stabilise a negative charge, a positive charge, a lone pair of electrons oran adjacent bond by resonance (i.e. delocalisation or ‘spreading out’ of the electrons). Curly arrows are usedto represent the movement of or non-bonding electrons to give different resonance forms. It is only theelectrons, not the nuclei, that move in the resonance forms and a double-headed arrow is used to show theirrelationship.


(a) Positive mesomeric effect:• When a -system donate electrons, the -system has a positive mesomeric effect (+M effect).

C CH

CHR

donate electrons:+M group

C CH

CHR

• When a lone pair of electrons is donated, the group donating the electrons has a positive mesomeric effect.

C OR

donates electrons:+M group

C OR

(b) Negative mesomeric effect:• When a system accepts electrons, the system has a negative mesomeric effect (–M effect).

C CH

CHR

Accept electrons:–M group

C CH

CHR

The actual structures of the cations or anions lie somewhere between the two resonace forms. All resonanceforms must have the same overall charge and obey the same rules of valency.

•• •• •••• ••••••••••••••

••••••••• •

In neutral compounds, there will always be a +M and –M groups(s):One group donates (+M) the electrons and the other group(s) accepts the electrons(–M).

RO CH

CHR RO CH CHR

+M group –M group

All resonance forms are not of the same energy. In phenol, for example, the resonance form which the intactaromatic benzene ring is expected to predominate.

OH OH OH OH+M group

–M grouparomaticring is intact

As a rule of thumb, the more resonance structures an anion, cation or neutral system can have, the morestable it is.

Inductive versus mesomeric effects:Mesomeric effects are generally stronger than inductive effects. A +M group is likely to stabilise an anion moreeffectively than a +I group.


Mesomeric effects can be effective over much longer distances than inductive effects, provided that conjuga-tion is present (i.e. alternating single and double bonds). Whereas inductive effects are determined by distance,mesomeric effects are determined by the relative positions of +M and –M groups in a molecule.

1.7. Resonance:The different structure of a compound divised by different methods of pairing electrons in a fixed atomicskeleton are called resonance of canonical structure. The actual structure of the compound is then a combina-tion of these structure and hence the compound is called a resonance hybrid. A hybrid is more stable than anyone of the contributing structures. The contributing resonance structure are shown by double-headed arrows

indicating that the real structures involves both way of pairing electrons.Key point about resonance:(i) Resonating structure/contributing structure/canonical structure are imaginary hypothetical, while resonance

hybrid is the true strucure.(ii) Resonance involve the delocalization of lone pair and -electrons.(iii) Resonance is the intramolecular process.(iv) Resonance must follow the Lewis octate rule, i.e. C-atom, N-atom never pentavalent and O-atom never

tetravalent.(v) In the resonating structure arrangement of atoms remain same, there should differ only w.r.to arrangement

of electrons.(vi) Resonance stabilisation is greatest, when there are equivalent resonating structure.

C

O

OR

O

OR

carboxylic ion

O O O O O

Phenoxide ion Resonance hybrid

(vii) The energy difference in between resonance hybrid and most stable resonating structure is called reso-nance energy

(viii) Resonance work only at ortho and para position with equal intensity, it never work at meta position.(ix) Resonance proceeds in the system via -electrons.(x) Hyper conjugation works just like resonance.

X

X

–Y–X

CH3

Nu–E

CH3

Nu

E


Classification of Resonance:(A) + R effect (B) –R effect(A) +R effect (Electron releasing effect):Lone pair of electron density containing compound attached with conjugation.

HO CH

CH2 HO CH

CH2

G

, G G = Electron Releasing Group

2 2–OH, – OR, NH , NR , O C

O

CH3 , NHC

CH3

O

, –F, –Cl, –Br, –I, –SH, etc

(B) –R effect (Electron withdrawing effect):Electronegative atom attached with multiple bond containing compound(a) Electron withdrawing resonance effectExample :

N

O

O

, C N , C

O, C

O

H, C

O

OH

H2C CH N

O

O

H2C CH NH

O

OH

(b) Species having Vacant d-orbitals

PMe3 PMe3

, PMe3 , , –SbMe3 , –SR2–AsMe3

(c) Species having vacant - p - orbitals:BR2 BR2

1.8. Application of inductive effect, hyperconjugation and mesomeric effect:Acidity and basicity:Acids: An acid is a substance that donates a proton (Bronsted-Lowry). Acidic compounds have low pKa-values and are good proton donors, as the anions (or conjugate bases), formed on the deprotonation, arerelatively stable.In water:

HA + H2OKa H3O + A is acidity constant

Acid Base Conjugate Acid Conjugate Basewhere, Ka


The more stable the conjugate base the stronger the acid

a 10 a3

aa

a2

pK log KH O AK The higher the value of K , the lower the HA

pK value and the more acidic is HAAs H O is in excess

The pKa-value equals the pH of the acid when it is half dissociated. At pH above the pKa the acid existspredominantly as the conjugate base in water. At pH below the pKa, it exists predominantly as HA.

pH 0 (strongly acidic)pH 7 (neutral)pH 14 (strongly basic)

The pKa-values are influenced by the solvent. Polar solvents will stabilise cations and/or anions by solvation,in which the charge is delocalised over the solvent (e.g. by hydrogen-bonding in water).

HO H A H OH

H2O O

H

H HOH2

The more electronegative the atom bearing the negative charge, the more stable the conjugate base (which isnegatively charged).

a

2 3 4

increasing electronegativity

3 16 33 48pKHF H O NH CHMost acidic

Therefore, F is more stable than H3C .The conjugate base can also be stabilised by –I and –M groups which can delocalise the negative charge.(The more spread out the negative charge, the more stable it is)

a

a

–I and –M groups therefore lower the pK , whileI and +M groups raise the pK

(a) Inductive effects and carboxylic acids:The carboxylate anion is formed on deprotonation of carboxylic acids. The anion is stabilised by resonance(i.e. the charge is spread over both oxygen atoms) but can also be stablised by the R group if this has a –Ieffect.

R CO

OH

Base

(–BaseH)R C

O

OR C

O

OThe greater the -I effect, the more stable the carboxylate anion and the more acidic is carboxylic acid.

F CH2 CO2H Br CH2 CO2H CH3 CO2H

2.7 2.9 4.8pKa

Most acidic as F is moreelectronegative than Br andhence has a greater –I effect

Least acidic as the CH3 group is a +I group


(b) Inductive and mesomeric effects and phenols:Mesomeric effects can also stabilise positive and negative charges.

arg – M arg M

The negative ch e needs to be on adjacent carbon atom for a group to estabilise itThe poisitive ch e needs to be on adjacent carbon atom for a group to stabilise it

On deprotonation of phenol the phenoxide anion is formed. This stabilised by delocalisation of the negativecharge at the 2-, 4-and 6-positions of the benzene ring.

OH O O O

Base

4

6 2

O

Temporary Effect :(a) Electromeric Effect :• Temporary effect.• Takes place between two atoms joined by a multiple bond• Occurs at requirement of attacking reagent.

C O + Z+ –

Instantaneous shift of electron pair of carbonyl group towards oxygen.It is of two types.(1) + E effect : Transition of electron towards the attacking reagent.

C C + H C C

H(2) –E effect :Transition of electron away from attacking reagent.

C O + CN CO

CN

(b) Inductomeric Effect ;• Temporary effect.• Takes place in sigma bonded system• In presence of attacking reagent, transition of a electron cloud takes place more readily.Example :

R O H + BIn presence of base B, movement of sigma electron takes place faster.

(3) Other Effect :(a) Effect of inertia/steric inhibition of resonance:Resonance ability of an atom is lost if it looses planarity with the other part of the system due to steric crowdingby bulky group in adjacent positions.


H3C CH3

NO2

NH2

NO2

NH2

(A) (B)

H3C CH3

The above two compounds A and B have everything identical except position of the two methyl group. It isexpected that A should be stronger base than B due to closeness of two electron donating methyl group to –NH2. The fact is opposite to this. In compound B –NO2 is surrounded by two bulky methyl group and theysterically repel the –NO2 group. In order to minimize the steric repulsion by the two adjacent methyl group, thenitro group loses planarity with the benzene ring. So, now –NO2 due to lack of planarity weigh ring, not able toresonate. This is known as steric inhibition of resonance. Thus in B , –NO2 is not decreasing basic strength byresonance. In A –NO2 lies in the plane of the ring, it is in resonance with the ring, decreases basic strength of–NH2 by resonance, hence weaker base.

Similarly we can explain the acidic strength of C and D

H3C CH3

NO2

COOH

NO2

COOH

(C) (D)

H3C CH3

C is stronger acid inspite of closeness of two electron donating methyl group to –COOH.

(b) Ortho effect: If any electron withdrawing group present on ortho position of the benzoic acid. It alwaysincreases acidic nature of acid because this group increases outer resonance of the ring toward acidic nature.Similarly if any group present on ortho position of aniline, it decreases basic nature. This effect is known asortho effect.Problem : The correct order of acidity among the following compound I-IV is

COOH COOHCOOH COOH

NO2

NO2

NO2

(I) (II) (III) (IV)

(a) II > III > IV > I (b) IV > II > III > I (c) II > IV > III > I (d) IV > III > II > ISoln. Because of ortho effect o-nitro benzoic acid is most acidic followed by para and meta.

Thus order will be II > IV > III > I.Hence, option (c) is correct.Keynotes in Organic Chemistry:• If –M groups are introduced at 2-, 4- and/or 6-positions, the anion can be further stabilised by delocalisation

through the system , as the negative charge can be spread onto the –M group. We can use double-headed curly arrows to show this process.


• If –M groups are introduced at the 3- and/or 5-positions, the anion can not be stabilised by delocalisation,as the negative charge cannot be spread onto the –M group. There is no way of using curly arrows todelocalise the charge onto the –M groups.

• If –I groups are introduced on the benzene ring, the effect will depend on their distance from the negativecharge. The closer the –I group is to the negative charge, the greater will be the stabilising effect . The orderof –I stabilisation is therefore 2-position > 3-position >4-position.

• The –M effects are much stronger than –I effects.

Example: The NO2 group is strongly electron-withdrawing; –I and –M.

The NO2 can only stabilise the anion inductively andby resonance

HO

4

6 2

OH OHHO

NO2NO2

NO2NO2

pKa 9.9 8.4 7.2 4.0Least acidic as no –I or –M groups on the ring

The NO2 can only stabilise the anion inductively

Most acidic as both NO2 groups can stabilise the anioninductively and by resonance

ON

N

O

O

OO

O

N

N

O

O

OO

O

N

N

O

O

OO

O

N

N

O

O

OO

The presence of groups such as OH, OMe, or halogen an electron-withdrawing inductive effect, but anelectron-donating mesomeric effect when in the o- and p- positions, may, however, cause the p- substitutedacids to be weaker than the m- and, on occasion, weaker even than the unsubstituted acid itself, e.g. p-hydroxybenzoic acid:

pK a of XC6H4CO2HH Cl Br OMe OHo-4.20 2.94 2.85 4.90 2.98m-4.20 3.83 3.81 4.09 4.08

–

+

OC

O

+

X

OC

O

Xp-4.20 3.99 4.00 4.47 4.58

It will be noticed that this compensating effect becomes more pronounced in going Cl Br OH, i.e.in increasing order of readiness with which the atom attached to the nucleus will part with its electron pairs.The behaviour of o- substituted acids is, as seen above, often anomalous. Their strength is sometimes foundto be considerably greater than expected due to direct interaction between the adjacent groups. Thusintramolecular hydrogen bonding stabilises the anion (4) from o-hydroxybenzoic (salicyclic) acid (3) bydelocalising its charge, an advantage not shared by its m- and p- isomers, nor by o- methoxy benzoic acid:


CO

HO

O H(3)

CO

HO

O(4)

–H+

–

Intramolecular hydrogen bonding can, of course, operate in the undissociated acid as well as in the anion,but it is likely to be considerably more effective in the latter than in the former - with consequent relativestabilisation - because the negative charge on oxygen in the anion will lead to stronger hydrogen bonding.The effect is even more pronounced where hydrogen bonding can occur with hydroxyl groups in both o-position, and 2, 6-dihydroxybenzoic acid is found to have pK a = 1.30.Dicarboxylic Acids:

HCO H2

CH CO H3 2

CH CH CO H3 2 2

C H CO H6 5 2

3.77

4.76

4.88

4.17

HO CCO H2 2

HO CCH CO H2 2 2

HO CCH CH CO H2 2 2 2

HO CC H CO H2 6 4 2

1.23

2.83

4.19

o m p- 2.98; - 3.46; - 3.51

Acid pKa Value Acid pKa Value

Bases: A base is a substance that accepts a proton (Bronsted-Lowry). Basic compounds have high pKa-values and are good proton acceptors, as the cations (or conjugate acids), formed on protonation, arerelatively stable.

In water:

B + H2O

KbBH + HO

where, Kb is basicity constantAcidBase Conjugate

AcidConjugate

BaseThe strength of bases are usually described by the Ka-and pKa-values of the conjugate acid.

+ H2OBHKa B + H3O where Ka is acidity constant.

2

3a As H O is in excess

B H OK

BH

• If B is a strong base, then BH will be relatively stable and not easily deprotonated. BH will thereforehave a high pKa-value

• If B is a weak base, then BH will be relatively unstable and easily deprotonated. BH will therefore havea low pKa-value.

The cation can be stabilised by +I and +M groups, which can delocalise the positive charge. (The more‘spread out’ the positive charge, the more stable it is).


(c) Inductive effects and aliphatic (or alkyl) amines: On protonation of amines, ammonium salts areformed.

R NH2 + H X R NH3 X

The greater the +I effect of the R group, the greater the electron density at nitrogen and the more basic theamine. The greater the +I effect, the more stable the ammonium cation and the more basic the amine.

N H

H

H

H N H

Et

H

Et N H

Et

H

Et N H

Et

H

Et

pKa 9.3 10.7 10.9 10.9

The pKa-values should increase steadily as more +I alkyl groups are introduced on nitrogen. However, thepKa-values are determined in water, and the more hydrogen atoms on the positively charged nitrogen, thegreater the extent of hydrogen-bonding between water and the cation. This solvation leads to the stabilisationof the cations containing N–H bonds.

In organic solvents (which can not solvate the cation), the order of pKas is expected to be as follows:

3 2 2 3most basic least basicR N R NH RNH NH R I alkyl group

The presence of –I and /or –M groups on nitrogen reduces the basicity, and hence, for example, amides arepoor bases.

Ethanamide has a pKa of –0.5.

C

O

NH2H3C

–M, –I

C

O

NH2H3C

The C=O group stabilisesthe lone pair on nitrogen byresonance. This reduces the electron density on nitrogen

(d) Mesomeric effects and aryl (or aromatic) amines:The lone pair of electrons on the nitrogen atom of aminobenzene (or aniline) can be stabilised by the delocalisationof the electrons onto the 2-, 4-and 6-positions of the benzene ring. Aromatic amines are therefore less basicthan aliphatic amines.

NH2

6 2

4

NH2 NH2 NH2

• If –M groups are introduced at the 2-, 4-and/or 6-positions (but not at the 3- or 5-position), the anion canbe further stabilised by delocalisation, as the negative charge can be spread onto the –M group. Thisreduces the basicity of the amine.

• If –I groups are introduced on the benzene ring, the order of –I stabilisation is 2-position > 3-position > 4-position. This reduces the basicity of the amine.


NH2 H2N NH2

NO2

NO2

pKa 4.6 2.45 –0.28

Most basic as no-I or –M groups on the ring

The NO2 group can stabilise the lone pair inductively

Least basic: The NO2 group can stabilisethe lone pair inductively and by resonance

• If +M group (e.g. OMe) are introduced at the 2-, 4- or 6-position of aminobenzene, then the basicity isincreased. This is because the +M group donates electron density to the carbon atom bearing the aminegroup.

H2N NH2 H2N

pKa 4.2 4.5 5.3Least basic: The OMe groupcannot donate electron density tothe carbon atom bearing the nitrongen

The OMe group can donate electrondensity to the nitrogen but it has a strong –I effect as it is in the 2-position

Most basic: The OMe group can donateelectron density to the nitrogen and it has a weak –I effect (as well apartfrom the nitrogen)

OMe

OMe

MeO

Curly arrows can be used to show the delocalisation of electrons onto the carbon atom bearing the nitrogen.

NH2 NH2 NH2

OMeOMe OMe

electron densityadjacent to the

nitrogen increasesthe basicity

(e) Lewis acids and base:• A Lewis acid is any substance that accepts an electron pair in forming a coordinate bond. Examples include

H+, BF3, AlCl3, TiCl4, ZnCl2 and SnCl4. They have unfilled valence shells and hence can accept electronpairs.

• A Lewis base is any substance that donates an electron pair in forming a coordinate bond. Examplesinclude H2O, ROH, RCHO, R2CO, R3N and R2S. They all have a lone pair(s) of electrons on the heteroatom (O, N or S)

C OR

R

Lewis base

Al Cl

Cl

Cl

C OR

RAl

Cl

Cl

Cl

Lewis acid

(f) Basicity and hybridisation:The greater the ‘s’ character of an orbital, the lower is energy the electrons and the more tightly the electronsare held to the nucleus. The electrons in an sp-orbital are therefore less available for protonation than those inan sp2- or sp3-hydrid orbital and hence the compounds are less basic.

most basic: R3N R2C NH RC N least basic

most basic: R3C R2C CH RC C least basic

> >

>>

sp3 sp2 sp(25%s) (33%s) (50%s)

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General Organic Chemistry - careerendeavour.in · General Organic Chemistry 5 Problem : The correct order for the stability among following compound is CH 3 CH 2 H 2 (II) (III) CH